Methanol → 1403899-01-3

HRID 1475317Notes

Reaction equation

HRID 1475317 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]3([CH2:13][CH2:12]3)[C:7](=O)[NH:8]2)=[CH:4][CH:3]=1.CO>C1COCC1>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]3([CH2:13][CH2:12]3)[CH2:7][NH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 726987906′-Chlorospiro[cyclopropane-1,3′-[3H]indol]-2′(1′H)-one

Product 1

HCID 726987911403899-01-3Yield 52.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6′ chloro-spiro[cyclopropane-1,3′-[3H]indol]-2′(1′H)-one (0.291 g, 1.5 mmol) and borane-dimethyl sulfide complex in THF (2 M, 3.0 mL) was heated at reflux under nitrogen for 2 h. The mixture was cooled and MeOH (3 mL) was added dropwise (caution!). The resulting mixture was heated at reflux for 2 h, then was cooled and solvent evaporated in vacuo. Chromatography (SiO2; gradient elution with 0-100% Et2O in petrol) gave the title compound (0.142 g). MS: [M+H]+=180.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 2 h
  3. temperatureThe mixture was cooled
  4. temperatureThe resulting mixture was heated
  5. temperatureat reflux for 2 h
  6. temperaturewas cooled
  7. customsolvent evaporated in vacuo
  8. washChromatography (SiO2; gradient elution with 0-100% Et2O in petrol)

Sources & evidence

ORD record
ord-591e33db7ac24a28b307ca4401e38525
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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